The Ultimate Beginners Guide to Sailing and Rafting

The Ultimate Beginners Guide to Sailing and Rafting

Sailing is one of those hobbies that can seem out of reach for many. It can almost appear to be a hobby saved for the prestigious and ‘Bill Gates‘ of people out there. But, we’re here to tell you it couldn’t be farther from the truth. In fact, you can teach yourself to sail using the principles of sailing and a very large glossary. 

So, here at The Hobby Kraze, our team have been hard at work making sure everything is covered in this beginner’s guide to learn sailing and rafting. Because, a hobby better than sailing out into the great blue world is rafting up with like-minded sailing friends and creating one huge boat party. 

Whether you’re heading into the middle of a lake with some sailing fanatics or enjoying the calm turquoise oceans off the coast of a hot Mediterranean country, putting together the principles of sailing as well as the mooring guidelines, you’ll be set for an incredible hobby adventure.

With that, have a look at all the fun and interesting factors of learning the principles of sailing and rafting up with this ultimate beginner’s guide to sailing and rafting:

  1. Why You Should Consider Taking Up Sailing and Rafting as a Hobby
  2. How the Principles of Sailing Came About as a Hobby
  3. The Beginner’s Guide to Sailing and Rafting’s A to Z of a Boat
  4. Teaching Yourself to Sail by Having all the Necessary Tools and Equipment
  5. Understanding the Points of Sail
  6. Prepping Your Sailboat for Shoving Off
  7. Understanding How to Begin Rafting Up for a Secure Boat Party
  8. The Best Places in the World to Be Rafting up with Your Friends

One thing we will mention before shoving off from the jetty is that sailing boats can come with or without motors. But, as a responsible supporter of our environment (and your pocket) the team here at The Hobby Kraze have been tasked with providing you all the know-how about using the sail. A.K.A. boating without a motor and finding out where the wind will take you next.

Why You Should Consider Taking Up Sailing and Rafting as a Hobby

As we’ve already mentioned, taking up a sailing hobby isn’t as expensive as it originally sounds. In fact, it will generally cost the same amount as taking up photography and videography when you consider lights, lenses and all sorts. 

And, it’s not as complex as everyone might imagine, either. While a boat isn’t as simple as a car moving forward and back, the controls of having sails and the wind can pretty much account for a simpler day out.

Therefore, if you like to be out on the water but don’t necessarily want to put in the effort for stand-up paddle boarding or kayaking and love to stay above water-level, then sailing is for you. The Hobby Kraze crew has put together a list of all the reasons you should try the hobby of sailing and rafting, today:

  • It is very calming
  • It is an easy hobby to pick up once the glossary is mastered
  • It can be enjoyed alone or with friends and family
  • You can incorporate sailing and rafting for a boat party
  • Sailing lets out the endorphins
  • It keeps your mind active
  • Sailing can help prevent the effects of dementia
  • You can hire boats instead of buying boats
  • Obtaining a boating license to hire can be short and fun
  • You can meet like-minded enthusiasts just on the jetty
  • You can travel anywhere the water takes you
  • You can enjoy your new hobby anywhere in the world
  • It helps to improve your flexibility and agility
  • You’ll be lugging heavy equipment that makes you stronger
  • You can venture into other avenues such as racing or competitive adventuring

How the Principles of Sailing Came About as a Hobby

How the Principles of Sailing Came About as a Hobby

Humans have been using boats for thousands of years and can even be dated back to Egyptian activity on the River Nile for goods and trade movement. 

Then, the earliest notion of using sails and wind for propulsion comes from the time of the Vikings. Despite sounding mythological, they truly ventured and conquered with their Viking longboats and dragon-adorned bow.

Yet, it wasn’t until thousands of years later in the 15th century when advancements would enable longer trips. These enhanced journeys allowed for exploration and colonisation of new worlds such as; Australia, New Zealand and America.

After long haul travel by sail became possible, new ways to conquer the Earth were opened up. And, in 1519, the Spanish set sail for a course around the world. A course, which would eventually take two captains and four years to complete. 

Since then, the keel (a structural beam running under the boat from bow to stern), the lateen (a triangular sail) and marine engines have all been strives that brought us to modern day sailing. While materials may have changed and parts of the boat may have become sturdier, the beauty of this hobby is that it is an ancient trade. And, you can be next to carry on the tradition.

Then, rafting up to other boats came naturally when ships would trade mid-sea or get together to moor safely and enjoy the company of others. And, that’s why this beginner’s guide to sailing and rafting wanted to cover rafting as part of the sailing hobby; to interact and enjoy your boating passions with others.

However, strides in the sailing community continue to be made. With new GPS devices as well as more accessible races and regattas, there’s always a new component to look forward to. So, let’s find out what principles of sailing can be unearthed in this beginner’s guide to sailing and rafting. 

The Beginner’s Guide to Sailing and Rafting’s A to Z of a Boat

The Beginner’s Guide to Sailing and Rafting’s A to Z of a Boat

In this beginner’s guide to sailing and rafting, we have to let you know that most of being able to sail a boat comes from understanding the never-ending glossary of terms. In fact, when you know the parts of a boat and what the jargon means, you’ll know what to do with them and how they’ll work in the principles of sailing. 

For example; a skipper is an individual who pilots a ship and controls the crew. You’ll have one on hire if you ever charter a boat without intending to sail it yourself. However, hiring a person as well as a boat can be a little more expensive. So, we suggest skipping the skipper and trying to teach yourself to sail with this beginner’s guide to sailing and rafting.

So, to get you started, we’ve gathered the essential A to Z of terms, tools and equipment you’ll be facing in your new hobby adventure on the sea.

    • Cockpit

The cockpit is the area where the captain will stay. It is within the mid-deck and will often feature the helm or tiller for steering. In very transferrable fashion; the cockpit relates to the hub of control.

    • Tiller

This is a long device that will protrude into your cockpit at an angle suitable to control. This is because it connects to the rudder on the underside of the boat and is used to steer in sailing.

    • Rudder

The rudder is a protrusion underneath the boat, Sometimes, there can be three rudders or just one controlling the boat depending on the size and width. The rudder will connect to either a tiller or helm on the cockpit and can be controlled by the captain.

    • Hull

This is the watertight encasing for the ship. It is the body and the name given to any water-sporting device, such as the body of a kayak or stand-up paddle board. The hull of a ship will have a deck on top to cover. And, the line where water meet’s the hull is called the waterline.

    • Helm

A helm is a steering wheel for your boat, much like the ones you’d see in a pirate movie but a little smaller. These are often in place of the tiller as they control the boat through manoeuvring the rudder.

    • Mast

The mast is the large metal and wood stick protruding from the mid-deck of the boat. It is in front of the cockpit and is the vertical bearer for the boom and sails.

    • Boom

The boom is another very thick metal and wooden bar that is parallel with the deck of the ship and stems in a perpendicular manner from the mast. It holds the main sail and will also be the base for encasing the main sail when not in use. It will also have a kicker attached at the bottom.

    • Sheet 

In any boating sport or hobby, the principles of sailing may change traditional terminology. For example; the ropes on a sailing boat are not called ropes as soon as they have a use. Each rope is then called a sheet and is given a purpose. Loose rope is still, however, called rope. You may hear phrases such as; “pull in the main sheet” or “let out the main sheet” which tells you to ‘trim’ (put tension on) the rope attached to your main sail.

    • Winch

On both the port and starboard sides of the ship, there are round winches that kind of look like a thread bobbin from a sewing machine (see The Ultimate Beginner’s Guide to Sewing for more!). The sheet from the head sail will get wrapped around the winches for control and stability.

    • Rigging

Rigging is the incorporation of various sheets all around your vessel in order to support the mast. These might be all the ropes and swings that make the sailing and rafting hobby look harder than it actually is.

    • Backstay

The backstay is the name given to the rigging located at the back of the boat or vessel. 

    • Shrouds

Much like the backstay, this is the name given to rigging and sheets located in the middle of the boat around the area of the cockpit.

    • Forestay

Also called the jib stay, the forestay is the rigging at the bow and foredeck of your sailboat. It is also called the jib stay because it is the rigging that helps the jib sail remain secure.

    • Head Sail

The head sail (A.K.A. the jib sail) is the sail that sits at the bow of the boat in front of the main mast. It attaches to the forestay and two roller blocks either side of the boat. This sail can be 100% in size to cover the full triangular area between the mast and the forestay, or it can be bigger such as a 130% named a Genoa.

    • Roller Furling

At the bottom of the forestay, there is a spinning drum named the roller furling. While not every forestay or boat will have one, the drum helps to spin the sail up and wrap it for easy access.

    • Bow/foredeck

The bow of a ship is also named the foredeck and refers to the front of the ship where the forestay and head sail are located. There is often a point at the tip of the ship for aerodynamic optimisation.

    • Stern

The stern is the opposite of the bow where the backstay and rudder are located. It’s important the rudder steers from the stern to help minimise drifting. 

    • Halyard 

The halyard is a very specific and important sheet that connects to everything. The halyard sits at the top of the mast and is connected to both the main sail and the head sail. It is used to raise and lower both the sails when in the open water.

    • Dock Lines

Dock lines are very thick and very strong sheets that are used to attach your boat to the mooring guidelines and posts at the jetty in the marina or harbour. When you begin rafting up after you teach yourself to sail, instead of dock lines, you’ll use mooring lines. These lines are much longer and are used to attach boats together and to a buoy where required.

    • Track

Both the mast, the forestay and the backstay will have a small metal track that runs vertically upward. It is indented to the mast and is where the runner of the sail will sit to help keep it secure and in place when raised or lowered.

    • Head, Tack and Clew

There are three parts to a sail. If you imagine a right-angled triangle, the head is the top 45-degree angle. The tack is the 90-degree right-angle that sits in the corner. And, the clew is the bottom 45-degree angle. Both the head and the tack will be attached to either the mast or forestay and the clew and tack will be attached either to the boom or to clutches either side of the ship.

    • Clutch

Either side of the boat, on starboard and port, there will either be a clutch or a roller block. These will be situated in front of the winches. They are designed to hold the sheets attached to the clew of the head sail in place.

    • Starboard

As you may have guessed in the rest of this beginner’s guide to sailing and rafting glossary, the starboard is one side of the boat. In fact, starboard refers to the right-hand side.

    • Port

When one side has a name, so must the other. The port side of the vessel is the left-hand side.

    • Oar 

Even though the sailboat uses sails and wind to propel forward, they still need help in momentum and steering from time-to-time. Especially when manoeuvring the marina’s berth. So, you’ll often find a very large oar sticking out the back of your boat. Or, located at the side and ready to be prepared for movement. Some boats use a motor, but an oar is easier, cheaper and better for our oceans. 

    • Kicker (metal attachment to stop the boom from rising up the mast)

At the bottom of the boom and where it attaches to the mast, there is a very strong metal and wood kicker. It attaches both the ship’s necessities together and prevents the boom from rising up the mast.

Teaching Yourself to Sail by Having all the Necessary Tools and Equipment

Teaching Yourself to Sail by Having all the Necessary Tools and Equipment

It’s not just the boat that needs to be equipped for your first day in the open water. There’s many tools and equipment that you’ll need, too. With it being the hobby for both the lone ranger and the social magnet, there’s tools and equipment that you’ll need on board to keep everyone safe. 

Here at The Hobby Kraze we like to make sure that everyone is not only enjoying their hobby but making sure they’re aware of all the risk prevention methods for their hobby, too. That’s why it might seem strange to have tools such as a fire extinguisher on board a ship surrounded by water, but you’ll be surprised at how many ship fires can take down a crew. 

  • Personal Floatation Device
  • Compass
  • Phone
  • Power Bank Charger
  • 4G MiFi Device
  • Fire Extinguisher
  • Torch
  • Water
  • Food
  • Dry Clothes
  • Throwable PFD
  • Sound Signalling Device
  • Whistle
  • First Aid Kit
  • Anchor
  • Snorkel
  • Mask
  • Oar
  • Knife
  • ID
  • Suntan Lotion
  • Sunglasses
  • Radar Reflector
  • Binoculars
  • Flare
  • Fenders
  • Extra Mooring Lines
  • Booze for Guests

A final thing to consider within this beginner’s guide to sailing and rafting is the world we live in. With modern technology and social media, making memories has changed into storing memories. So, a top tip from the team here at The Hobby Kraze is to always take a small camera with you. Whether it’s a smart phone, GoPro or Osmo Pocket, make sure you’ve got all the gear to watch back the memories of the calm blue ocean and times spent rafting up with your friends.

Understanding the Points of Sail

Understanding the Points of Sail

No matter where in the world you decide to set sail, you’ll always need to know and understand the principles of sailing by revising the points of sail. Knowing exactly how the wind will affect your direction, speed and ability to begin rafting up with others is vital in your expedition to hobby happiness. 

In reality, there are five points of sail and a few more directional terms you’ll need to know. And, it involves picturing a clock. Or, a pie; whichever sails your boat. For now, we’ll being with the points of sail:

    • The No-Go Zone 

Also known as ‘going in irons’, this refers to your boat being stopped due to the way you are positioned on the clock.

Taking the analogy of the clock, your wind is coming from 12 O’clock. It takes up about ¼ of your clock. If you’re heading windward in the no-go zone, your sails will be luffing and the boat will not have any momentum to move forward, if you need to travel in the direction of the wind’s origin, then you’ll have to start tacking for beam reach either-side in order to not stall.

    • Close-Hauled/Close-Reach

Just outside of the direction of the wind (around 2 O’clock if we’re going clockwise) is called travelling at close-hauled. At this point you should start tacking and winching everything tight in order to move forward. Top tip; if this all seems a little complicated now, it will become far simpler when your aboard and practicing sailing.

    • Beam Reach

At beam-reach you can picture yourself moving towards 3 O’clock if you’re travelling port side and toward 9 O’clock if you’re travelling starboard side. When travelling at beam-reach, you can loosen your winches but do make sure to tie everything down otherwise the contents of your cabin might begin weighing one side of the ship down.

  • Broad Reach

At around 4 O’clock and 5 O’clock, you’ll be travelling at broad reach. And, this is often argued to be the best point of sail, especially when you teach yourself to sail. This is because it offers good thrusting power, but you won’t be travelling as fast as when you’re running. Whatever you do, make sure you don’t gybe; you or one of your guests will end-up swimming home.

  • Running

The fifth and final point of sail, as mentioned, is running. At this point on the clock you’re dead-on 6 O’clock and you’re officially travelling leeward. As the wind is behind the sail, the sails will act as a parachute and you’ll be travelling ahead with ease. However, as this is the ultimate beginner’s guide to sailing and rafting, we would advise against the high-speed effects of travelling leeward.

 So, that’s the points of sail covered. Now, we can get moving onto the other directions and movements you should know while working as a skipper on deck while you teach yourself to sail. 

  • Windward

Travelling windward is, quite simply, travelling in the direction of the wind’s origin. So, if we think about the clock and wind coming in from 12 O’clock, you’re heading to 12 O’clock. However, this is also ‘in irons’ and you’ll likely not be moving very fast unless you’re quick at tacking. 

  • Leeward

Leeward is the direct opposite of windward where you’ll be heading fore; away from the wind. 

  • Fore heading in the direction of the bow

When you’re described as heading ‘fore’, it means you’re heading in the direction of the bow of your sailboat. This applies for you on your boat as well as the movement on your boat. For example, your boat can be moored up or you could have been rafting up with other boats to keep static, but you’re moving around on your boat in the fore direction. 

  • Aft

Aft is the exact opposite of fore, in that the direction changes to the stern of the boat. For example; you’ll be travelling aft if you’re reversing into a berth. Or, you could be anchored and you’re travelling aft while walking on your boat.

  • Tacking and Gybing

Tacking and gybing (also known as jibing for the US captains out there) is the act of manoeuvring a sail. If you’re travelling windward, you’ll be tacking your sails side to side in order to find pace in the right direction. When travelling leeward, you’ll need to be gybing, but this can cause overboard casualties. Top tip from the crew here at The Hobby Kraze; you’ll want to practice being nimble and fast when tacking and gybing alongside mooring guidelines to get into a berth.

  • Give Way

Port tack gives way to starboard tack, or if you’re already part-taking in other sports such as Equestrian, you may know this as the ‘left-to-left’ rule. Keeping to these mooring guidelines and sailing etiquette can help save you time and money in your hobby as there’ll be far fewer crashes to contend with.

  • Berth (parking space)

While it’s not actually a manoeuvre, direction or point of sail, the berth is important to mention here because it is where you’ll park your vehicle. And, it will become a very important reference point between you, your crewmates, the harbour master and the marina operators. You may hear a phrase such as “head berth wise B12 upstream, starboard side”.

Prepping Your Sailboat for Shoving Off

Prepping Your Sailboat for Shoving Off

Before you can even begin to think about rafting up with other boats, you need to know the principles of sailing, shoving off and how the mooring guidelines will affect the way you sail before being free on the open water. 

To help with this, the team here at The Hobby Kraze have put together a play-by-play and to-do list for you to follow when you teach yourself to sail.

    1. Remove and store away the cover from the main sail on your boom.
    2. Grab the head (tip) of the main sale and place it within the mast’s track.
    3. Locate your halyard and thread it through the head of your main sail. 
    4. At this point, you’re not raising the main sail yet, you’re just getting it into position once you’ve left the marina and are clear of hazards or obstacles. So, pull the slack out of the halyard to get it ready.
    5. Get the head sail (also called the jib sail) out of the storage area in front of the mast.
    6. Carefully unfold the head sail onto the deck at the bow of the ship.
    7. Attach the tack of the head sail at the bottom of the forestay, near the deck.
    8. Then, place the head of the sail into the track of the forestay and pull it upwards.
    9. Take the halyard clip and connect to the head of the sail, ready for it to be pulled up when the wind is in.
    10. Pull on the halyard to remove the slack from the head sail. Again, we are not yet raising the sail, but instead getting into position.
    11. Top tip: use some loose rope to tie the headsail down onto the boat so it doesn’t fly into the water before raising the head sail and main sail.
    12. Tie the jib sheet onto the clew of the genoa headsail. To do this, simply fold the jib sheet in half, place the loop through the clew hole and then tread the two ends of the jib sheet into the new loop. Pull it tight to secure the sheet to the clew and you’ll be left with two jib sheet ends of equal lengths. 
    13. Take each jib sheet end to the outside of the shrouds so you have one end on starboard and the other on the port side of the boat. 
    14. Push the end of the jib sheet through a roller-block or clutch (whichever your boat has) and then tie a secure figure-of-8 knot in the end so it can’t be pulled back through. 
    15. Tidy the sheet ends by wrapping them around your forearm and hand so they aren’t all over the place.
    16. Head to the stern of your boat and ready your oar and tiller for shove off control.
    17. Remove all the dock lines or rafting up mooring lines and you’re ready to go.
    18. The final step would be to shove off from the jetty boardwalk, berth or the other boats. 

When it comes to mooring guidelines, they can very per the marina or harbour you decide to moor at. Often, with the rules regarding floating, you need to remain at around 5 to 10 knots and be very careful of other boats. You also need to be in constant contact with the marina guard when approaching or leaving the marina for safety. They’ll also be able to guide you to your berth if you’re not rafting up with other boats.

Understanding How to Begin Rafting Up for a Secure Boat Party

Understanding How to Begin Rafting Up for a Secure Boat Party

Finally, we’ve gotten to the most social and fun part of your beginner’s guide to sailing and rafting; finding out how to begin rafting up. 

Throughout this guide, we’ve been referring to ‘rafting up’ as something you’ll do in the middle of the open water with other boats in order to socialise and have fun while anchored. And, while this is very true and the most fun aspect to rafting up, it is not the only use. As sailing has become a more popular hobby available to many over the years, some marina hotspots may not have a berth for everyone. 

In these scenarios, it is very important to know your mooring guidelines and rafting up knots. You’ll need to raft to other boats in order to climb over and get to the jetty. 

However, it’s best to know how to raft up properly. Nobody wants to be woken at the crack of dawn by someone else in the raft trying to leave. And, it’s important to know how to deal with a mast mix-up after a heavy night with the weather. So, let’s talk about the different types of rafting up to help you get through any situation. A top tip from The Hobby Kraze team in this beginner’s guide to sailing and rafting is to always try and make friends with those you’ll be rafting up next to. A friendly encounter will always help with any miss-communications down the line. 

Whether it’s for the mid-lake boat party or for the over-crowded harbour, the first thing to do is make sure you have enough warps (mooring rope) and fenders (boat buoys, spacers and protectors). Then come close to someone that is on board (where possible) and request to raft up. Make sure they don’t need to leave too early otherwise you’ll be leaving that early, too.

Then, when you’re ready, begin to moor bow-to-stern (or, portside-to-portside). When rafting up to get to a jetty, you’ll need to make sure you’re not only attaching warps and sheets to your neighbour. For optimum security and minimal damage, make sure you’ve got shorelines to the heavy-duty cleats. If someone in the raft needs to leave early, make sure to not place a shoreline across their bow or in their chosen direction of travel. This way, they can leave and boats can adjust closer to the shore.

Finally, make sure all your sheet tail ends are wrapped up and stored on your own boat. It can be very rude to leave your messy ends all over the jetty or other people’s boats in the raft. Then, you’ll be set to move about, relax and socialise!

The Best Places in the World to Be Rafting up with Your Friends

The Best Places in the World to Be Rafting up with Your Friends

Now you’ve got all the equipment you need as well as the terms and know-how, you’re ready to shove off from the jetty (or the raft) and set sail. Whether it’s to meet up with friends, sink anchor and create your own raft or it’s to explore the wonderful water world this planet has to offer. 

With that, we couldn’t leave without giving you the ultimate beginner’s guide to sailing and rafting in the most beautiful and serene places our world has to offer. From rivers and lakes to the wide-open ocean; there’s a place to be sailing and a place to practice the mooring guidelines.

Check out some of the best places to spend your new sailing hobby knowledge:

  • Thailand
  • Greece
  • Scotland
  • Iceland
  • Australia
  • Italy
  • Spain
  • The French Riviera
  • Lake Geneva
  • Croatia
  • New Zealand
  • Jamaica
  • Grenada
  • St Lucia
  • Zanzibar
  • Montenegro
  • The Galapagos Islands
  • Norway
  • The North Pole
  • Hawaii
  • California
  • Rio de Janeiro


And, with that, it ends our ultimate beginner’s guide to sailing and rafting. But, there’s one last thing to note before heading off and mooring up. If you don’t have a boat, or a boat to borrow, you may want to consider trying out a sailing course. You’ll be able to gain a license with the principles of sailing and hire a boat anywhere around the world. And, if you have a sailing license in the UK, a new world of inland waterways and opportunities will open up for you to explore. 

As part of The Hobby Kraze’s series of water hobbies and recreational activities, try having a look at all the other fun and exciting sports you can do on the water. From; ‘The Ultimate Beginner’s Guide to Scuba Diving and Snorkelling’ to ‘The Ultimate Beginner’s Guide to Stand Up Paddle Boarding’, you’ll be able to find the hobby that suits you, your friends, your location and your budget.

We love to hear about your new hobby adventure, so if it’s to teach yourself to sail or any other hobby you choose, make sure to take pictures and videos and share them on social media with the crew at The Hobby Kraze.

P.S. Boats! Boats! Boats! (If you know, you know).

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Picture of Lisa Hayden-Matthews

Lisa Hayden-Matthews

An avid Skier, bike rider, triathlon enthusiast, amateurish beach volleyball player and nature lover who has never lost a dare! I manage the overall Editorial section for the magazine here and occasionally chip in with my own nature photographs, when required.
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